Syntheses of substituted 3-methyleneisoindolin-1-ones by a palladium-catalyzed Sonogashira coupling-carbonylation-hydroamination sequence in phosphonium salt-based ionic liquids.
Two efficient approaches for the synthesis of isoindolin-1-one derivatives in phosphonium salt ionic liquids are described. The palladium-catalyzed carbonylation-hydroamination reaction of 1-halo-2-alkynylbenzene with amines afforded the substituted 3-methyleneisoindolin-1-ones in good yields and high selectivities in favor of the Z-isomers. The target molecules could also be synthesized by the Sonogashira coupling-carbonylation-hydroamination one-pot reaction of dihalides, alkynes, and amines. Both processes can be conducted under mild conditions and tolerate a wide array of functionalized substrates.
Cao
Hong
H
Department of Chemistry, Centre for Catalysis Research and Innovation, University of Ottawa, Ottawa, Ontario, Canada.
McNamee
Laura
L
Alper
Howard
H
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D052578:Ionic Liquids / Q000737:chemistry*; D054833:Isoindoles / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
D000588:Amines; D052578:Ionic Liquids; D054833:Isoindoles; D009943:Organophosphorus Compounds; D010165:Palladium